[Update!] Took the plunge again and I am still shaking! [m/m] | 2016

Apologies all around for the delay in updating how things went in round 2 of taking the plunge into this surreal world of freakishly exhilarating mano a mano action. If you missed the backstory and context, you can find my original post here.

So, after our torrid first encounter, I was pretty much left in a wild mind-tailspin after I walked out his door to get to my car. Not in a bad way, normally when I’ve had these encounters before (albeit they are rare occasions), I usually feel twinges of regret, shame, “what the fuck were you thinking you idiot” type feelings. I’m sure some of you here can relate. However, this was entirely and wholly different, which was almost as terrifying.

While I promise I will regale you with the full nitty gritty details of the second rendezvous, I’ll be peppering in a lot of real talk, because as much as I love the idea of people getting off to the recounting of the encounter, I feel it does a disservice to the event if I don’t include the emotional context that is brewing with great, and somewhat frightening fervor throughout.

I offhandedly referred to my newest bedfellow as Alexander the Girth when my uvula was the Tina Turner to his mushroom head’s Ike. The name sort of stuck during our playful moments, and without giving too much personal info away, his name is indeed Alex, so I shall refer to him as such going forward.

Alex and I met for coffee the next morning, and it was simultaneously hella-weird, but also electrically invigorating. I say this, because while there was a very thick “holy shit, what happened last night” air hanging over the conversation, there was an equal, if not greater “lets get this over with and do it again!” compulsion driving the banter into more risqué and taboo territory. Which was fucking great. It was really quite fun to combine this awkward conversation with someone who made it quite clear that he wanted me to fuck his brains out like some lobotomized Randle McMurphy thrust-bot, and that this chat was the means to a very sticky and sweaty end.

However, we got along so well in these moments…that it actually set off some alarm bells I’ve never encountered before. As previously mentioned, my few encounters have been blow and go’s, where I was basically a fully-shamed Roger Bannister bolting out the door before both my pant legs were even on. Not so this time. Not so at all. I really like this guy. And I’m a guy. And I like a guy. Oh shit. We’re guys. And we like each other. Sure, we like the fucking and the sucking and the bathing in cum like it was manna sent from some veiny deity, but to actually feel attracted to both the physicality and personality of another dude…well, this was new territory for me. I’ve never identified as “gay” before, despite the unending thirst for gallons of genetic material, which I realize sounds oddly counter intuitive. But oh well. This was evolving into something that emotionally, I am STILL not sure what to think/feel.

Coffee wraps up, we both have some errands and things to do before hand, but agree to meet back at the scene of the crime (his place) at around 7 to “watch Netflix”. Fuck. Yes. I nearly give him a (public!) good bye kiss, which let me tell you, would have been just the biggest step outside my comfort zone ever, but no, instead I squeeze his ass in front of an elementary aged Vacation Bible School group that is occupying half the goddamn Starbucks. So, I’m thrilled my right hand and its proclivity for cheek squeezins will be the inspiration for some really eye opening dinner chats with their parents.

I pulled up to the house around 7 or 8 and I yell to the Uber, yo’ holmes, smell ya later. I look at his cock and he was finally there, as I sat on his bone as his mitts left me bare. Ok, none of that happened, I just drove my Honda on time, and he lives in an apartment. But I did bring a 12 pack of Shiner Bock, this being Texas, and he is only 19, so I AM AN ENABLER OF ILLICIT ACTIVITIES.

Now, let it be known that Alex, despite the 2-liter Mr. Pibb bottle he keeps attached to his pelvis, that looks shockingly penis like, and his tenacious “fuck me like a school girl” power-bottoming, is an old-soul. On more than one-occasion, he, despite his youth, has fulfilled my own personal silver-daddy fetish by throwing out the occasional Perry Como reference in conversation. I swear if I dug deep enough into the closet he is currently hiding in, I would find a Rydell High ’58 letterman jacket back there. I say all this because even though our situation is something generally progressive and…non-traditional, he is still outstandingly chivalrous and well-mannered. Also, hung. But the anachronism of the situation is oddly endearing.

He let me in, I present beer, he does not even acknowledge it, and immediately grabs my dick through my very nice shorts, which had little embroidered lobsters all over them. There was no mention of the beer or the lobsters, which is regrettable, however, my cock is being given all the attention, which I find most agreeable. He leads me to the couch, and there is an odd abatement in our physical journey, and we actually do watch Netflix, but we chat…and he puts his head on my chest, and we honest to God watch an episode of Frasier. I love Frasier, so at this point, I’m all in. We talk, we laugh, we joke, it is very relationship-y, and were this a girl, I’d think I had this chick in the bag and I had a new g/f and we were well on our way to Facebook official town. But its a guy. And he feels the same way about me. What. The. Fuck.

The emotionality of all this made each sweeping motion of his hand on my body (still head on chest, watching Netflix) feel like he was holding a goddamn bug zapper. I started getting really tingly like I had Denorex on half my scalp, and I have butterflies all over. Which is odd, considering it had not even been 24 hours since I went Mama Cass all over his dick and followed that up by shooting a Balthazar worth of cum on his prostate. But still, the fire is alive and well.

It turns out that not all hands who wander are lost, and he made his way down my lobster shorts, unbuckled my belt, and unbuttoned the button with one-hand. The sheer physical achievement shown in this moment was a huge turn-on, and he very gingerly walked his fingers over to my cock, which at this point was hard enough to help drill for iron ore. If you remember my previous post, Alex is a seductive moaner. That’s his super power, he does these little baby moans when something strikes his fancy, and its like goddamn catnip to me. I can’t get enough. So when he puts his hand around my cock, he lets out an excited little moan. He is just as excited as me that this is happening. And that is fucking hot. Also, sidenote, I was so engorged at this moment that when he held my dick tight, I could feel my pulse in my cock. That’s a level of horny that should unlock some achievement badge. DICKTACULAR.

I raise my ass up off the couch slightly, and with his one disturbingly dextrous right hand, he pulls everything down to the floor, and dives in towards my granite-hard cock, which given my pulse, probably felt like a Sonicare in his mouth. He takes great care to make a show of licking it from base to tip, turning his head to make eye contact with me as he sucks and kisses and tastes it with glee. There is enough pre-cum leaking out of me at this point that dehydration might become an issue, and my moans are not nearly as subtle and delicate as his. But again, this didn’t feel like a stranger, this felt like a guy I liked…and the game was very much changed.

I could still smell the shampoo in his hair as it bobbed up and down below me, and I knew Alex as freshly showered, so this gave me some unusual amounts of gumption for upping the ante. I pull his face up towards mine, my pre-cum still wet on his tongue, and we make out, as we are often wont to do, and I taste myself in him. Which really gets me going. I suggest we make our way over to his bed, as I felt like we had reached the limit of what the couch would allow us to do. He obliged, and as he grabs my hand to let me to his bed, I stop cold, realizing he still has clothes on, and that will not suffice. So I grab him from behind, start kissing his neck, running my hands all over him, down to his cock and all over his ass, take off his shirt, kiss his back, pull off his mesh shorts (no undies), and I don’t leave a single square inch untouched. I pop back up, walk over to the bed, push him down on his back, and tell him to bring his knees up towards his chest.

Now, what I begin to do, I had never done before. I’ve received it, but never had the impetus to deliver unto someone. But I get down on my hands and knees, start kissing down his stomach, liking and sucking his cock briefly, and then I slowly rub my finger on his asshole…all of a sudden his typical dainty-moans became infinitely less subtle. From there, I take my new plunge, and take my tongue and flick it against the rim of his hole, and finishing each lick in an upwards motion that hits the bottom of his balls. It goes from flick to slurp in a matter of seconds. I jam my tongue as far inside as I could, and it was clean as a whistle. I knew he was preparing to get fucked again, and evidently chivalry includes a high colonic or something, because it was like the ground floor of Fort Knox in there, tight and clean as hell. I do this for a while and he is leaking like a sieve. I take a quick breather, and he grabs my hair and pulls me up to his face, where he puts both hands on my face and begins to kiss me and suck my tongue like he was trying to pull out snake venom to save my life. It was so. fucking. hot. I know rimming isn’t for everyone, and we’d previously swapped cum like we were casually trading Pogs at summer camp, but no, this was a new level of “holy shit I cannot get more turned on” right now.

I have always identified as more of a top, mostly out of fear, but now with Alex, I was open to broadening all my horizons. Many of you reading this I feel, want to try out way more than you allow yourself to do in your A4A/Manhunt/Grindr/CL hookups, which is totes understandable. What made this situation great was, our comfortability gave me the courage to drop those fears and…quite literally…go nuts. I had bottomed before, once for a teacher when I was a senior in HS…that’s a story for another time, jesus. But I was willing to give it a go.

Fortunately, Alex had a few toys, and I knew I needed to stretch myself out a bit before trying to take his Turvis Tumbler sized meat pipe into my cobwebbed trademan’s entrance. He didn’t have a giant selection, but he did have a decently large donger with a flared base, because there is no fucking way I am going to the ER just to see a dildo floating around my descending colon on an X-ray while a gaggle of wide-eyed med students furiously take down notes and secretly Snapchat my pain for their friends amusement. So, we used a flared one.

Alex applies about 10 pints of lube on my hole, fingering me with great aplomb as he does it, and slides in the stand-in butt plug, as I let out several cries and grab his arm. He asks if he should stop, but I decline, because, it hurts…but its hurts so good. I am lying on my back, and he starts working it in and around my asshole. He shifts slightly, and puts his knees near the side of my head, as he leans and continues working. I reach up and start stroking his cock, which i am just staring at while my ass it getting some practice work, and he leans down and put it squarely in my mouth. I. love. his cock. There is no way around it. I wish I had a detachable version of it that I could keep like a vascular Tamagotchi on my keys, because I’d suck it to completion every 10 minutes if I could. Sucking Alex off while he stretched my asshole was pretty much the zenith of sexual nirvana at this moment. My prostate getting just brutalized while I taste all the pre-cum this sweet pineapple eating prince could muster. I was ready.

Alex very gently removes Frankie-the-Faux-Dick from me, and I can already feel my asshole allowing more air inside. Praise Jesus, because otherwise he would split me in two and my ass would look like a cross sectional view at a Body World’s exhibit. I am instructed to get on all fours, and I eagerly do what I am told. Alex informs me that his dick needs some lubrication, and before I can answer, it puts it in front of my mouth like I’m some angler-fish who uses dicks to lure in my food. I open wide, suck him for a minute, and he nods and pats me on the head. We both laugh at the absurdity of all this. That laughter immediately is murdered as I feel his hands grab my hips, and I spread my cheeks with everything I have, and I feel the tip of his cock start rubbing on my hole. Holy shit. This is happening.

Alex gingerly forces in the tip, and I yell out “FUCK”, while hitting the headboard with a closed hand. He presses onward, slowly, but unrelentingly. It just kept going. Its like watching a shitty magician who keeps pulling out a 10 mile long handkerchief out of a vagabond’s luggage, except it’s Alex’s penis and my asshole is the vagabond’s luggage. Which is a sentence I never thought I’d type. Once my hole begins to accommodate the girth of the situation, Alex turns up the heat. He times his thrusts with the pulling back of my hips, and I feel like I am being punished in the best way possible. He slaps my ass several times while fucking the shit out of me, and demands that I tell him if I like it. The feeling I have at this moment is like when you first jump into cold water, and you have no breath with which to speak. Well, in this moment, I am being so vigorously fucked, and the feelings so intense, I can’t really say much. I hope with all the fibers in my being he doesn’t cum too fast, because I am riding this thin-line of euphoria that it honestly feels like I am on drugs. I can’t think straight, I can barely talk, I can’t stop moaning, I think I have tears in my eyes, I am shaking, I am rock fucking hard, I am doing everything I can to hold on for dear life as this 19 year old kid just unleashes everything his porpoise-sized dick can throw at me, and it’s as if I am bull riding just hoping to survive the adrenaline rush and not fall off.

Alex sensed that my moans were the most ear-piercing things he’d heard from me yet, and he pumps the brakes a bit…and I finally exhale. I moan out “please fuck me, oh my god please fuck me, fuck daddy.” We had never discussed role play before, so it was a little out of left field the daddy thing, but he went with it. What had been thrusts from the back of a 19 year old Falcon rocket, became very slow, but incredibly deep thrusts. It felt like my entire ass was filled with his cock, like there was no room for anything else. I figured that when he came, it would just shoot out my nose because surely there was no room left in there. It was an amazing feeling, particularly at the apex of his thrust, knowing that Alex was so completely inside me. Again, the emotionality of our relationship was causing the physicality of it to be kicked into an overdrive I have never really experienced before, especially when combined with the newness and taboo nature of our situation.

Alex flipped me on my back, and he continued the slow but Armageddon-drill-team-deep exploration into my ass, and stared right at me as he did it. He was trying to look tough, but as I found the strength to squeeze my ass a bit, I could see a wry smile cross his face as the waves of pleasures washed over his cock as he continued fucking me senseless. He would lean down and kiss me, suck on my tongue, and thrust again deeper and deeper. Having a guy put all over his weight into his cock as it sinks entirely into your ass while he sucks your tongue and licks your lips and asks “do you like that?”, I mean, fuck, man. How can you not be gay?

I begin to squeeze my ass more and more, and try and milk his cock as he moves in and out, and I can tell he is close. His wry smile disappears, and his eyes close, he is concentrating, or at least trying to. I get a wave of chutzpah and I wrap my legs around his waist, pull him in hard, and tell him to fuck me and punish me. He turns on the afterburners, and my ass is split wide open, now with the fast thrusts but with the depth of the slow-power ones. I keep holding onto him with my legs, and I can feel in his rhythm that he is close, and as I watch his face, I give one final squeeze with my ass on his cock, and he just exploded. Rope after rope after rope of cum is blown into my ass, I can see Alex shaking as he just keeps cumming. He removes his dick and I can just feel the cum dripping from my hole, and it rolls down towards my lower back. It felt like someone did the gallon challenge except with my butthole. Or whatever was left of it.

Alex decided to just go for broke, tells me to bring my knees to my chest, and starts sucking my dick…and in a fit of madness, I feel him flick my hole with his tongue. All the same maneuvers I did to him earlier, he does to me, my freshly fucked, still dripping with his cum, asshole. I moan like a little bitch just at the thought of how hot this is, and he licks and licks and probes, and I know I am close. He doesn’t even have to touch my dick, this whole thing is way too filthy and hot to need dick friction for a climax. I tell him I am close, and he takes one giant lick, from the bottom of my hole, across it, up my balls, and with his cum from my ass in his mouth, takes in my cock, and I unleash a lifetime’s worth of cum against the back of his throat. When I open my eyes I half expect him to look like this.

True to our nature, he swallows most of it, and starts kissing me, and we share an amalgam of both our cum and god knows what the hell else. My ass feels like someone put a sticky M80 in it, and the lingering effects of my climax I think gave all my joints spontaneous rheumatoid arthritis. We laid there, him on my chest, and just marveled at what all just happened. And in somewhat adorable fashion, after just the most animalistic gay ass-fucking imaginable, he looks up at me at one point and tells me that “ya know, i think i really “like” like you”, sheepishly. I tell him I share this opinion, and that I actually think I am developing normal, human, relational feelings for him. Less robotic sounding than that, but you get the picture.

Incredibly long story short, I spend the night…and that is fucking awesome. No more ass fucking, because I would probably be dead, but we blow each other several more times randomly throughout the evening, and we sleep naked together in a spooning position, my cock wedged against his ass. I often found myself just reaching over and playing with his dick and balls and kissing his neck and back whenever, and he couldn’t have been happier.

I woke up to him licking my dick trying to get it hard without waking me, and he had mostly succeeded. I’ll admit to you all, that I might have pretended to be asleep a little longer than I let on to him, but eventually I opened one eye and watched him with incredible zeal and excitement suck my cock to start the day…and i “woke up” just in time to tell him I was going to cum…I spurt all over his open mouth, he shows me it, swallows most of it, kisses me, then touched my face sweetly and thanked me for breakfast.

I dare say, I think I might be smitten.